Diols such as 1,3-butanediol and 1,4-butanediol and esters such as butyl acetate and propyl acetate are industrially useful as solvents and raw material chemicals, and have been used in various fields as plastic raw materials, cosmetics, flavors, fragrances, and the like.
Such a diol has been manufactured by reaction of an alkyne such as acetylene with an aldehyde followed by hydrogenation of the product, or by diacetoxylation of a diene compound such as butadiene followed by reduction and hydrolysis. However, acetylene has problems in terms of safety and stable availability.
Meanwhile, as a method for manufacturing an ester, a method is known in which a carboxylic acid and an alcohol are reacted with each other in the presence of an acid catalyst. Moreover, J. Am. Chem. Soc., 2005, vol. 127, p. 6970 to 6971 (NPL 1) and J. Am. Chem. Soc., 2004, vol. 126, p. 1346 to 1347 (NPL 2) disclose that ester compounds having an α,β-unsaturated bond can be obtained by reactions of acetic acid with various terminal olefins in a sulfoxide solvent such as dimethyl sulfoxide in the presence of a palladium catalyst and an oxidizing agent such as benzoquinone.
Terminal olefins can be esterified by the method described in NPL 1 or 2. However, since internal olefins and cyclic olefins have low reactivities, it is difficult to obtain by these methods ester compounds having an α,β-unsaturated bond at relatively high yields by using these olefins as raw materials. In addition, when a mixture olefin containing not only a terminal olefin, but also an internal olefin or a cyclic olefin is used as a raw material, there is a problem that only the terminal olefin is esterified, and the internal olefin or the cyclic olefin remains unreacted.
Meanwhile, Angew. Chem. Int. Ed., 2006, vol. 45, p. 481 to 485 (NPL 3) discloses that ester compounds having an α,β-unsaturated bond can be obtained by reactions of acetic acid with various terminal olefins in N,N-dimethylacetamide in the presence of a palladium catalyst and sodium acetate.